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Lake Street Dive’s ascent from its music school roots to Manhattan’s largest concert stage is a story of an old-fashioned work ethic in an era of overnight TikTok stars. 

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A decade ago, when Lake Street Dive performed in New York City, it played the 600-capacity Bowery Ballroom, a notch on the belt for up-and-coming acts. Not long before that, the band, which came together in 2004 at the New England School Conservatory of Music, played gigs at the cozy Rockwood Music Hall, wine bar-cum-music venue that could squeeze a couple hundred people at its biggest stage. In 2022, Lake Street Dive had taken its brand of pop-meets-jazz-meets-soul to two nights at Radio City Music Hall.

By 2024, the five-piece band was ready for the city’s most vaunted stage, the 19,500-capacity Madison Square Garden. Thinking about performing at the historic arena, which has hosted everything from the legendary Concert for Bangladesh in 1971 to a 10-year Billy Joel residency, gave singer Rachael Price “a fair amount of imposter syndrome,” she tells Billboard’s Behind the Setlist podcast. 

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“But when we got there and we walked out on stage, and we felt the crowd, it was like every single person had seen us play at Rockwood Music Hall. That’s how they felt. The energy of the faces in the crowd, they all had this like knowing look on their face, [as if they were saying,] ‘I’ve seen you in this city for 10 years, and I knew you guys when.’ And so the whole thing felt kind of like a big homecoming. It felt like a graduation party.”

Drummer Mike Calabrese found himself with a similarly weak stomach before the show. “I didn’t sleep the night before, and I was nauseous all day until sound check,” he says. ”But then I realized, oh yeah, our fans are the best. We’ve played New York a million times. We know what we’re doing. Everything’s fine.”

Price, Calabrese and their bandmates — bass player Bridget Kearney, keyboardist Akie Bermiss and guitarist James Cornelison — reached another career milestone in 2024 when their eighth studio album, Good Together, was nominated for a Grammy for best traditional pop vocal album. For a self-described “genre-less band,” receiving a nomination that typically requires being placed into a genre came as a surprise. “We definitely have all said to each other — maybe to ourselves —[that] we will never get nominated for a Grammy,” says Price.

Success has a way of finding talented artists who persevere, though, and Lake Street Dive has put in the hard work to merit both a Madison Square Garden gig and a Grammy nod. “We have been doing this for 20 years — and steadily for 20 years,” says Calabrese. “And I’m not saying that everybody who does that for 20 years deserves a Grammy necessarily, but it’s very exciting, and we’re very honored. I also feel like we made a really good album. It would be one thing if we were a band that was one or two years on the scene and had this just massive hit and boom!”

Still, the Grammy nomination was so unexpected that the band didn’t contemplate leaving time in their tour schedule to attend the ceremony in Los Angeles on Feb. 2. “It wasn’t on our bingo card,” admits Price. Instead, the band will be enjoying a day off in Amsterdam while touring in Europe. “If someone wants to send their private plane to get us there — which we’re against philosophically — then we would go,” she jokes. 

Listen to the entire interview with Rachel Price and Mike Calabrese below, or go to Spotify, Apple Podcasts, Amazon Music, iHeart, Audible, Podbean or Everand.